


Wildest Dreams

by cozypancakes



Category: Community (TV)
Genre: M/M, Romance, Smut, but lucky for him that is exactly the reality they are in, light humor, the dean cannot fathom a reality where Jeffrey Winger wants to have sex with him
Language: English
Status: Completed
Published: 2020-05-15
Updated: 2020-05-15
Packaged: 2021-03-02 20:40:55
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,778
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24192982
Author URL: https://archiveofourown.org/users/cozypancakes/pseuds/cozypancakes
Summary: The Dean wakes up in his bed, naked, with an equally naked Jeffrey Winger beside him. The only possible explanation is that Craig has officially lost his mind and is hallucinating...right?
Relationships: Dean Craig Pelton/Jeff Winger
Comments: 17
Kudos: 169





	Wildest Dreams

**Author's Note:**

> I'm 99% certain I've read all the Dean/Jeff fanfic out there so now I am forced to make my own. Hope you enjoy!

The sunlight is what woke him up. He blinked rapidly as he lifted his head to look at his window. Odd, he always closed the curtains before going to bed. He must have forgotten to last night. He’d only had one drink, but obviously that had had more of an effect than he realized. He snuggled into his pillow and closed his eyes again. Though he could tell that sleep would be hard to come by.

His mind was flooding with memories of his dreams. Of course, they’d featured Jeffrey Winger. It had been a while since Craig had experienced such vivid and naughty dreams about the professor. Craig smiled as he let his mind remember. If he couldn’t go back to sleep, then he might as well relive the dream and have some fun. His eyebrows furrowed. Wait...was he...naked? Craig opened his eyes and grabbed his glasses from the nightstand. He lifted the sheet. Yes, he was most definitely naked. How odd. He almost never slept naked, always preferring a comfortable and lacy nightgown or booty shorts. 

Craig was already about to flip onto his back to ponder how many drinks he’d  _ really _ had last night when the bed shifted under a weight that was not his own. Next thing he knew, an arm, a very muscular and tan arm, was wrapped across his waist and a warmth enveloped his back. Craig’s heart was racing a mile a minute. Oh dear, what the hell had happened last night? Who was this man next to him? Why was he naked? Oh no, no, no. 

Like a deer caught in headlights, Craig was frozen to his spot. He tried to take several calming breaths, forcing his mind not to think about murderers and drugs slipped into drinks. After what felt like an eternity but was probably closer to a few minutes, Craig finally got the nerve to turn around and see who else was in his bed. Slowly, so as not to wake his companion, he turned his upper body. When he got a look at the face resting angelically on his pillow, Craig did the most logical thing possible: he screamed and fell off the bed. 

* * *

_ They’d gone out for drinks. It was almost a weekly occurrence now. And would probably continue to be so as long as Britta kept this bartending gig. Craig always looked forward to these nights. Not only because he always managed to secure a seat next to Jeffrey, but because he enjoyed spending time with the people he considered his closest friends. The conversation was always light, catching up on the gossip of Greendale and making fun of students or each other.  _

_ Some nights, they’d get absolutely plastered and make too much commotion. Those days had its perks because Craig could throw himself at Jeffrey, not even having to feign clumsiness. And Jeffrey, equally drunk, would wrap his arms around Craig and get them a taxi and reach into Craig’s pockets to fish out his keys for his apartment.  _

_ Tonight was not one of those nights. The atmosphere was relaxed and everyone sipped at their drinks as they recounted their week. Drunk or not, it had become customary for him and Jeffrey to share a cab back to their apartment building. So much so, that when Jeffrey looked over at him, Craig knew exactly what he was asking and nodded. They bid the others farewell and Craig’s heart did a small somersault when Jeffrey mindless helped him into his coat.  _

* * *

Craig fell to the floor with a loud thud. “What? What? What’s wrong?” He heard from the bed. Craig struggled to sit up with his legs tangled in the sheet. He poked his head over the mattress and saw a startled, and very much naked, Jeffrey Winger. Craig knew that Jeffrey was waiting for a response but his eyes couldn’t help but be distracted by the naked god in front of him. Craig could feel his vision begin to blur, a fainting spell coming on. 

Jeffrey snapped his fingers in front of Craig’s face. Craig blinked a few times and then forced his eyes to stare at Jeffrey’s face. “Are you alright?” Jeffrey asked. Craig nodded. Jeffrey looked at his face a moment longer. Craig wanted to swoon when he realized that Jeffrey was worried about him. Seemingly satisfied that Craig was uninjured, Jeffrey fell back on the bed and flung an arm over his eyes. “Since you’re out of bed, would you mind closing the curtains? Too early,” Jeffrey mumbled. His gruff voice was doing intense things to Craig’s body. Since his brain hadn’t quite caught up with the absurdity of the situation, Craig did as he was told, keeping a firm grip on the blanket covering his body. When the curtains were closed, Craig turned back and his mind short circuited. 

Jeffrey Winger was spread out on his bed in all his naked glory. Craig’s eyes roamed over his gorgeous muscles, to his pert nipples, down his abs, and stopped at his groin. Though flaccid, the sight of Jeffrey’s cock made Craig’s mouth water. And for whatever reason, that was the thing that rebooted Craig’s brain. 

“We had sex!” he squealed. His eyes moved back up to Jeffrey’s face with shock. Jeffrey moved his arm and smirked up at Craig. 

“Yeah, we did,” Jeffrey commented. Craig stared at Jeffrey. Most of his daydreams and fantasies had never really gone past the sex part. Though the few times he did consider what the aftermath would be, he’d imagined Jeffrey turning cold, dressing quickly, and leaving the room with great urgency. Jeffrey seemed to have no intention of getting off the bed. And there wasn’t any shame or regret or repulsion in his features. 

That and the fact that  _ he’d had sex with Jeffrey _ were really messing with his ability to form any other sentence that wasn’t, “We had sex…” This time, Jeffrey raised an elegant eyebrow at him. 

“Yes, and if you come back to bed we could do it again,” Jeffrey said. Craig was fairly certain that he was about to pass out at any moment. 

“It’s finally happened,” Craig mumbled. He looked off into nothing as his brain tried to wrap around this reality. “I’ve finally lost my mind.” He had been aware that his obsession with Jeffrey wasn’t exactly “healthy”. Sure, some things he would exaggerate for the comedic effect, but he’d been pining after this man for years! Obviously his mind was desperately trying to give him what he wanted and had formed this oddly realistic hallucination. That was the only explanation. 

* * *

_ The cab rides back to their apartment building were always some of the best parts of Craig’s week. It wasn’t a terribly long ride, but these moments of having Jeffrey’s undivided attention were incredible. Usually they kept the conversation from the bar going or would, good naturedly, talk about the group of friends they’d left at the bar.  _

_ Tonight was particularly nice. Jeffrey’s laughs came easily and he never once cringed away when Craig would pat his shoulder or arm. Craig had noticed that Jeffrey was slowly surrendering the fight against all the little touches Craig snuck in whenever he could. It would hardly be considered a victory to anyone else, but to Craig it was the world.  _

_ When they got out of the taxi, Craig, feeling bold, wrapped his hand around Jeffrey’s arm. He was expecting to be shrugged off, but Jeffrey looked down at him and shook his head. Craig liked to believe he saw an adoring smile on his face. Either way, Jeffrey allowed the contact all the way up to their apartment doors.  _

_ Craig knew better than to try and pretend he was too drunk to get his own keys. He turned towards his door and opened it easily. He was ready to bid Jeffrey a good night when a hand gripped his arm. He was turned around and held in place as Jeffrey grabbed both his upper arms. Craig was very confused. He looked up at Jeffrey and tilted his head to the side, asking a silent question. He watched as Jeffrey took in a big breath of air. Then, Craig was being pulled towards Jeffrey and Jeffrey was leaning down towards him. Craig’s mind went blank for a millisecond and then all he could feel were Jeffrey’s warm lips against his. He’d pictured and dreamed of this moment countless times. This exact moment: Jeffrey, kissing him in front of his apartment. It was so familiar to Craig. So when Jeffrey pulled away from the gentle kiss and looked into Craig’s eyes. Craig did what he’d done hundreds of times before. He pulled Jeffrey down by the collar of his shirt and kissed him hard. Because naturally this was another one of his dreams. And Craig would be damned if he didn’t take full advantage of the present his subconscious was giving him.  _

* * *

Craig closed his eyes and pinched his arm, in case that would wake him up. He looked back to his bed and wanted to cry. There was Jeffrey, still naked, though now sitting up and giving him a concerned look. 

“Craig...what’s wrong?” Jeffrey asked. 

“You’re not real,” Craig responded. 

“What are you talking about?”

“You’re not real!” Craig repeated. He started pacing, panicking. “At first, I thought it was merely a dream; you kissing me. I’ve had dozens of them. But now, it’s morning and you’re still here and I’m wide awake and I don’t know what to do.” His voice had gotten more shrill with each sentence he spoke. He was lost in his thoughts so he jumped when Jeffrey grabbed his arms. 

“Craig, breath!” Jeffrey demanded. Craig shut his eyes and tried to even out his breathing. It took a few minutes but Craig focused on Jefrrey’s thumbs rubbing soothing circles on his arms. “Are you calm now?” Jeffrey asked. Craig nodded. “Okay, now what do you mean you thought it was a dream?” 

Craig rolled his eyes. For a figment of his imagination, this Jeffrey was not the smartest. “Well, of course Jeffrey would never in a million years kiss me,” he stated the obvious. 

Jeffrey was staring at him. “Craig,” he began, “I am the real Jeff.” Craig gave him a look that clearly stated that was a cute but unbelievable attempt at getting Craig to believe this. Jeffrey let out a deep sigh. “This is Abed all over again…” he mumbled under his breath. Craig watched Jeffrey look around the room, searching for something. “Alright,” Jeffrey said, eyes back on Craig’s face. “If I’m a figment of your imagination, why can I touch you?” 

Craig scoffed.”Come on, Jeffrey, that’s an easy one. Haven’t you ever seen season 5 of  _ Grey’s Anatomy _ ? Oh god, do I have cancer?” Craig clutched his heart. 

“No!” Jeffrey yelled. “You don’t have cancer, because I am  _ not  _ a hallucination.” Jeffrey ran his hand through his hair, clearly frustrated. Craig wanted to reach out and comfort Jeffrey. Hallucination or not, he hated seeing Jeffrey upset. “Ah!” Jeffrey exclaimed. Craig jumped in surprise. Jeffrey ran over to the other side of the room, searching the floor. “Where…oh!” He quickly turned around and walked out of the room. Craig stood where he was, extremely confused. Should he follow Jeffrey? What if this was the end of the hallucination? As much as Craig did not want to be losing his mind, or have cancer, he didn’t want naked Jeffrey to disappear either. 

Craig was ready to run out of the room when Jeffrey returned. “Here!” Jeffrey proclaimed. He held up a phone in his hand. “If I was a hallucination, then I wouldn’t show up in a photo, right?” Jeffrey didn’t wait for an explanation. He pulled Craig towards him and took a quick selfie. Jeffrey shoved the phone into Craig’s hand. “See!” Craig looked down at the phone. It certainly felt solid. Then he focused on the picture. There he was, hand clutching the bed sheet, an extremely confused look on his face, and then there was Jeffrey, annoyed expression adding to the hotness. 

Craig stared at the photo and then looked back up at Jeffrey. His gaze returned to the photo. “But-”

“Say I’m a hallucination one more time and I swear to God, Craig!” Jeffrey walked until they were toe to toe together and then reached up and flicked his forehead. 

“Ow,” Craig complained. He rubbed his forehead and stared at Jeffrey. “You’re really not a hallucination…”

“I’m not!” Jeffrey ground out through clenched teeth. 

“Then that means...we…”

“Had sex, yes,” Jeffrey said. 

“Oh,” Craig replied. He felt faint again. He started remembering last night with a whole new perspective. “I can’t believe all of that really happened,” he whispered. 

“Um, what exactly do you remember?” Jeffrey asked. “So that we’re on the same page.”

Craig would have been offended by the question if he hadn’t accused Jeffrey of being a figment of his imagination not two minutes ago. “Well,  _ you  _ kissed me in the hallway?”

Jeffrey rolled his eyes at the question. “Yes, I did.”

“Why?” 

Craig watched as Jeffrey was caught off guard by the question. But Craig had to ask. Maybe then he could convince himself that this was reality. He didn’t know what he wanted the answer to be. Had Jeffrey been drunk? Had it been a dare that’d gotten out of hand? Had he been questioning his sexuality and used willing Craig as a way to experiment? 

“I…” Jeff cleared his throat, looking anywhere other than Craig. After a pause, Jeffrey returned his gaze to Craig. “I wanted to.” Craig wanted time to overanalyze Jeffrey’s answer. There was obviously a longer answer to it that Craig was dying to know. But then Jeffrey said, “After I kissed you, you nearly choked me pulling me down for a second kiss.” There was a teasing note to his voice and his lips seemed to be fighting back a smile. 

He playful swatted Jeffrey’s arm. “Can you blame me for being enthusiastic?” 

“I suppose not, I  _ am  _ really hot,” Jeffrey teased, an arrogant smirk taking over his face. Craig could stare at that face for hours. 

“Yes, you are,” Craig replied. He pushed his luck and let his eyes wander down Jeffrey’s naked body. He slowly dragged his eyes back up to Jeffrey’s face and was surprised to see Jeffrey biting down on his bottom lip.

“What else do you remember?” Jeffrey asked, his voice hoarse. 

Craig swallowed. Was Jeffrey really turned on right now? Because of him? “I...I remember we came into the apartment. You pushed me against a wall and we kept kissing.” Craig was reliving the moment in his head. Now that he knew it was real...Craig could feel himself begin to harden under the bed sheet. “You started grinding against me, hands wandering over me.”

“And you kept making these hot little sounds,” Jeffrey added. 

“Oh?” Craig gasped. He was definitely hard now. 

“Yeah, I really enjoyed making you moan. I wanted you to scream my name.”

“Well..you sure were able to accomplish that,” Craig reminded him. 

“I don't know,” Jeffrey pondered. He stepped into Craig’s personal space, one hand coming up to land on his hip. Craig could feel the heat burning him through the bedsheet. Then Jeffrey began rubbing circles into his hip with his thumb and Craig saw stars. “You were pretty convinced that I was a dream.” Jeffrey’s other hand moved to mirror his movements. Craig could barely hear Jeffrey’s words over the pounding of his heart. “How good could I have been if you thought that was a dream? Did I not blow your mind? Did you not wake up sore and aching?” 

“Jeffrey…” Craig whimpered. By the time Craig realized Jeffrey had been guiding him back towards the bed, Jeffrey was already shoving him onto the mattress. Jeffrey then yanked the bed sheet away to reveal Craig’s naked body. Craig looked up at Jeffrey staring down at him and oh god, Jeffrey was hard. Knowing he had that kind of affect on Jeffrey was completely electrifying. Craig could feel his whole body pulse with the need to be fucked. It was all too much. Craig shivered and his back arched simply because Jeffrey’s eyes were on him.

* * *

_ They were a mess of fumbling limbs and messy kisses. Jeffrey hadn’t even bothered to unbutton Craig’s shirt. He simply ripped it off, sending buttons flying all over Craig’s hallway. Craig wasn’t even bothered with the fact that Jeffrey took much better care of unbuttoning his own shirt. He simply wanted to have Jeffrey shirtless. And boy was that a sight to see. Even in the unlit bedroom, Craig was awestruck by Jeffrey’s chiseled chest. Craig ran his hand all over abs and pectorals. Jeffrey groaned when his finger brushed a nipple. Craig made a mental note of that; something to include in future fantasies.  _

_ Even though this was Craig’s room, he was still surprised when the back of his legs hit his bed. He sat at the edge of his bed, fingers hesitating around Jeffrey’s belt. He looked up at the other man, wondering if this was the point where he’d wake up. Jeffrey nodded his head, shifting his hips into Craig’s palm. Craig stopped worrying about when this might end and eagerly removed Jeffrey’s pants. Craig wasn’t surprised by the colorfully striped underwear. He had seen Jeffrey in various states of undress over the years. He was floored by the pronounced erection tenting the underwear. Craig reached out and gently ran his fingers over the erection. Jeffrey groaned above him, leaning into his touch again.  _

_ It was all the encouragement Craig needed. He slid Jeffrey’s underwear off and wasted no time in placing his mouth over the head of Jeffrey’s cock. Jeffrey’s hands rested on the back of Craig’s neck and Craig began to move his head up and down.  _

_ “Fuck Craig!” Jeffrey moaned. His hold on Craig’s head tightened, spurring Craig on to suck him off more. He was already imagining how good it would feel to taste Jeffrey’s cum when he was suddenly pushed away. Jeffrey kept his hand firmly on Craig’s shoulder as he panted for breath. “We don’t want things to end so soon,” Jeffrey explained. “So take your pants off and get on the bed.” Craig was only too happy to oblige.  _

* * *

Jeffrey took his sweet time getting on the bed and laying his body on top of his. Slowly, Jeffrey leaned down and brushed his lips against Craig. Craig moaned in frustration. “Obviously I’m going to have to do a much better job of fucking you this time. Until there is no doubt in your mind that this is real.” 

“Yes,” Craig groaned. 

And Jeffrey finally kissed him properly. He pushed his tongue into Craig’s mouth. Craig moaned and whimpered under Jeffrey. Jeffrey got lost in the kiss and let his body fall completely on top of Craig, their erections rubbing against each other. Craig’s hips began to move of their own accord. The feeling of Jeffrey’s cock on his, at least one of them already leaking precum, was incredible. Craig wrapped his legs around Jeffrey’s hips, needing him closer. Jeffrey moved from his mouth to trail kisses down his throat. Craig lost all restraint when Jeffrey bit down on his neck. 

“Oh, Jeffrey...fuck, yes...shit!” Craig moaned. He was lost in the pleasure. Jeffrey shifted their bodies so he could reach over to the nightstand for more lube. He coated his fingers in the slippery substance and quickly inserted two into Craig’s opening. The shock of the cold liquid entering his overheated body had Craig arching off the bed. Jeffrey kept mouthing at his chest, occasionally licking and teasing a nipple. His fingers stretched Craig open and would randomly send waves of pleasure down his spine as he’d graze his prostate. Craig knew it was random because Jeffrey lacked some skill in finding the spot. But Craig was in no mood to let Jeffrey practice right now. “Please, fuck, Jeffrey, please,” he pleaded. 

Jeffrey took mercy on him. He removed his fingers and reached back over to the nightstand for a condom. Craig watched with blatant enjoyment as Jeffrey put on the condom and poured lube on his hard cock. Even if this was the last time they ever fucked, Craig would always have this memory for his lonely nights. 

“Ready?” Jeffrey asked. Craig felt tears spring to his eyes. Who knew Jeffrey would be such a considerate lover? Even last night, Jeffrey had been so gentle as he’d fingered him open for the first time. Craig nodded, not trusting his voice at the moment. Jeffrey shifted his muscled body and Craig felt as Jeffrey entered him. It was easier than it had been last night. Jeffrey slid in with almost no resistance. Craig moaned out as he was filled. He could feel Jeffrey trembling above him and took great pride in the fact that he wasn’t the only one so affected. When Jeffrey took a second too long to start moving, Craig clenched down around him. 

“Fuck!” Jeffrey groaned. He buried his face in Craig’s neck and bit him lightly in retaliation. 

“Jeffrey, please, fuck me,” Craig begged. Jeffrey’s hips stuttered forward at his plea. And then they started moving in earnest. Last night had begun hesitant and unsure. Today Jeffrey’s confidence had obviously grown because he quickly started pounding into Craig with abandon. Craig clung to Jeffrey’s back, nails biting into skin. He let his moan and groans ring out as loudly as he wanted. “Yes, yes, fuck Jeffrey,” Craig began to babble. “God your cock is so big and so good. Yes, fuck me harder.” Jeffrey’s hands tightened on the sheets beneath them. His hips increased their speed, his breathing coming out in short gasps. “That’s it, just like that. Make me sore, so sore I can’t sit down for days.” 

“Shit, fuck,” Jeffrey groaned against his neck. 

For whatever reason, that was the hottest thing Craig had ever heard. His orgasm hit him with the realization that he was driving Jeffrey Winger crazy with desire. His vision was barely beginning to clear up when he felt Jeffrey tense above him. The feeling of Jeffrey’s cock pulsing inside of him nearly did Craig in again. 

Jeffrey collapsed on top of him and Craig was more than happy with this arrangement. He patted at Jeffrey’s hair, trying to regain his breath. Criag may not have thought he was dreaming anymore, but surely he had died and gone to heaven. 


End file.
